#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/64/2236455.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2236455
loop_
_publ_author_name
'Wei, Shuai-Shuai'
'Jin, Shou-Wen'
'Dong, Qiong'
'Cao, Xin-Chao'
'Yu, Ze-Yun'
_publ_section_title
;
 Bis(2-methyl-1H-benzimidazol-3-ium) naphthalene-1,5-disulfonate
;
_journal_coeditor_code           LH5531
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2964
_journal_paper_doi               10.1107/S1600536812039396
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '2C8 H9 N2 + , C10 H6 O6 S2 2-'
_chemical_formula_moiety         '2(C8 H9 N2), C10 H6 O6 S2'
_chemical_formula_sum            'C26 H24 N4 O6 S2'
_chemical_formula_weight         552.61
_chemical_name_systematic
;
Bis(2-methyl-1H-benzimidazol-3-ium) naphthalene-1,5-disulfonate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                105.7890(10)
_cell_angle_beta                 103.3030(10)
_cell_angle_gamma                106.497(2)
_cell_formula_units_Z            1
_cell_length_a                   8.0360(7)
_cell_length_b                   9.3969(8)
_cell_length_c                   9.5101(9)
_cell_measurement_reflns_used    1471
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.022
_cell_measurement_theta_min      2.361
_cell_volume                     624.75(10)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0529
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3137
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_T_min  0.888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.372
_refine_ls_extinction_coef       0.043(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2169
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0583P)²+0.1477P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1191
_reflns_number_gt                1694
_reflns_number_total             2169
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5531.cif
_cod_data_source_block           I
_cod_database_code               2236455
_cod_database_fobs_code          2236455
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
N N1 0.2089(3) 0.0991(2) -0.0901(2) 0.0390(5) Uani d . 1 1
H H1 0.1838 0.1027 -0.1817 0.047 Uiso calc R 1 1
N N2 0.2562(3) 0.1632(2) 0.1561(2) 0.0404(5) Uani d . 1 1
H H2 0.2664 0.2148 0.2495 0.048 Uiso calc R 1 1
O O1 0.3057(3) 0.2484(2) 0.4604(2) 0.0530(6) Uani d . 1 1
O O2 0.1946(3) 0.1418(2) 0.6381(2) 0.0447(5) Uani d . 1 1
O O3 0.4010(3) 0.4162(2) 0.7288(2) 0.0524(5) Uani d . 1 1
S S1 0.25771(8) 0.28337(7) 0.60043(6) 0.0330(2) Uani d . 1 1
C C1 0.2166(4) 0.2092(3) 0.0356(3) 0.0383(6) Uani d . 1 1
C C2 0.2784(3) 0.0185(3) 0.1067(3) 0.0354(6) Uani d . 1 1
C C3 0.2475(3) -0.0230(3) -0.0511(3) 0.0354(6) Uani d . 1 1
C C4 0.2607(4) -0.1614(3) -0.1376(3) 0.0436(7) Uani d . 1 1
H H4 0.2379 -0.1902 -0.2438 0.052 Uiso calc R 1 1
C C5 0.3095(4) -0.2543(3) -0.0584(3) 0.0495(7) Uani d . 1 1
H H5 0.3195 -0.3484 -0.1125 0.059 Uiso calc R 1 1
C C6 0.3443(4) -0.2105(3) 0.1010(3) 0.0497(7) Uani d . 1 1
H H6 0.3796 -0.2751 0.1506 0.060 Uiso calc R 1 1
C C7 0.3281(4) -0.0747(3) 0.1870(3) 0.0455(7) Uani d . 1 1
H H7 0.3493 -0.0467 0.2929 0.055 Uiso calc R 1 1
C C8 0.1861(4) 0.3582(3) 0.0410(4) 0.0552(8) Uani d . 1 1
H H8A 0.1993 0.4176 0.1452 0.083 Uiso calc PR 0.50 1
H H8B 0.0643 0.3332 -0.0263 0.083 Uiso calc PR 0.50 1
H H8C 0.2749 0.4206 0.0077 0.083 Uiso calc PR 0.50 1
H H8D 0.1597 0.3633 -0.0608 0.083 Uiso calc PR 0.50 1
H H8E 0.2947 0.4477 0.1106 0.083 Uiso calc PR 0.50 1
H H8F 0.0841 0.3603 0.0767 0.083 Uiso calc PR 0.50 1
C C9 -0.0943(3) 0.2568(3) 0.5733(3) 0.0356(6) Uani d . 1 1
H H9 -0.1013 0.1681 0.6009 0.043 Uiso calc R 1 1
C C10 0.0652(3) 0.3429(3) 0.5591(2) 0.0284(5) Uani d . 1 1
C C11 0.0793(3) 0.4782(3) 0.5137(2) 0.0275(5) Uani d . 1 1
C C12 0.2405(3) 0.5702(3) 0.4963(3) 0.0336(6) Uani d . 1 1
H H12 0.3438 0.5427 0.5143 0.040 Uiso calc R 1 1
C C13 0.2477(3) 0.6986(3) 0.4535(3) 0.0388(6) Uani d . 1 1
H H13 0.3552 0.7570 0.4421 0.047 Uiso calc R 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C1 N1 C3 . . 109.56(19)
C1 N1 H1 . . 125.2
C3 N1 H1 . . 125.2
C1 N2 C2 . . 109.1(2)
C1 N2 H2 . . 125.5
C2 N2 H2 . . 125.5
O3 S1 O1 . . 112.92(13)
O3 S1 O2 . . 113.16(11)
O1 S1 O2 . . 111.54(11)
O3 S1 C10 . . 106.00(11)
O1 S1 C10 . . 106.50(10)
O2 S1 C10 . . 106.07(11)
N1 C1 N2 . . 108.8(2)
N1 C1 C8 . . 125.5(2)
N2 C1 C8 . . 125.7(2)
C3 C2 N2 . . 106.4(2)
C3 C2 C7 . . 121.8(2)
N2 C2 C7 . . 131.7(2)
C4 C3 C2 . . 121.7(2)
C4 C3 N1 . . 132.2(2)
C2 C3 N1 . . 106.1(2)
C5 C4 C3 . . 116.6(2)
C5 C4 H4 . . 121.7
C3 C4 H4 . . 121.7
C4 C5 C6 . . 121.5(3)
C4 C5 H5 . . 119.2
C6 C5 H5 . . 119.2
C7 C6 C5 . . 122.0(3)
C7 C6 H6 . . 119.0
C5 C6 H6 . . 119.0
C6 C7 C2 . . 116.2(2)
C6 C7 H7 . . 121.9
C2 C7 H7 . . 121.9
C1 C8 H8A . . 109.5
C1 C8 H8B . . 109.5
H8A C8 H8B . . 109.5
C1 C8 H8C . . 109.5
H8A C8 H8C . . 109.5
H8B C8 H8C . . 109.5
C1 C8 H8D . . 109.5
H8A C8 H8D . . 141.1
H8B C8 H8D . . 56.3
H8C C8 H8D . . 56.3
C1 C8 H8E . . 109.5
H8A C8 H8E . . 56.3
H8B C8 H8E . . 141.1
H8C C8 H8E . . 56.3
H8D C8 H8E . . 109.5
C1 C8 H8F . . 109.5
H8A C8 H8F . . 56.3
H8B C8 H8F . . 56.3
H8C C8 H8F . . 141.1
H8D C8 H8F . . 109.5
H8E C8 H8F . . 109.5
C10 C9 C13 . 2_566 120.3(2)
C10 C9 H9 . . 119.8
C13 C9 H9 2_566 . 119.8
C9 C10 C11 . . 121.2(2)
C9 C10 S1 . . 118.13(18)
C11 C10 S1 . . 120.63(17)
C12 C11 C10 . . 123.4(2)
C12 C11 C11 . 2_566 118.9(2)
C10 C11 C11 . 2_566 117.7(3)
C13 C12 C11 . . 121.3(2)
C13 C12 H12 . . 119.4
C11 C12 H12 . . 119.4
C12 C13 C9 . 2_566 120.5(2)
C12 C13 H13 . . 119.7
C9 C13 H13 2_566 . 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C1 . 1.327(3)
N1 C3 . 1.390(3)
N1 H1 . 0.8600
N2 C1 . 1.335(3)
N2 C2 . 1.389(3)
N2 H2 . 0.8600
O1 S1 . 1.4491(17)
O2 S1 . 1.4543(17)
O3 S1 . 1.4427(19)
S1 C10 . 1.786(2)
C1 C8 . 1.478(4)
C2 C3 . 1.386(3)
C2 C7 . 1.390(4)
C3 C4 . 1.384(3)
C4 C5 . 1.378(4)
C4 H4 . 0.9300
C5 C6 . 1.395(4)
C5 H5 . 0.9300
C6 C7 . 1.375(4)
C6 H6 . 0.9300
C7 H7 . 0.9300
C8 H8A . 0.9600
C8 H8B . 0.9600
C8 H8C . 0.9600
C8 H8D . 0.9600
C8 H8E . 0.9600
C8 H8F . 0.9600
C9 C10 . 1.366(3)
C9 C13 2_566 1.403(4)
C9 H9 . 0.9300
C10 C11 . 1.433(3)
C11 C12 . 1.413(3)
C11 C11 2_566 1.436(4)
C12 C13 . 1.365(3)
C12 H12 . 0.9300
C13 C9 2_566 1.403(4)
C13 H13 . 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 O2 1_554 0.86 1.86 2.704(3) 165
N2 H2 O1 . 0.86 1.88 2.684(3) 155
C8 H8E O3 2_666 0.96 2.32 3.230(4) 158
C4 H4 Cg1 2_555 0.93 2.61 3.468(3) 154
C4 H4 Cg2 1_544 0.93 2.61 3.468(3) 154
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C3 N1 C1 N2 . . -1.0(3)
C3 N1 C1 C8 . . 179.1(3)
C2 N2 C1 N1 . . 1.1(3)
C2 N2 C1 C8 . . -178.9(3)
C1 N2 C2 C3 . . -0.9(3)
C1 N2 C2 C7 . . 176.6(3)
N2 C2 C3 C4 . . 179.3(2)
C7 C2 C3 C4 . . 1.5(4)
N2 C2 C3 N1 . . 0.3(3)
C7 C2 C3 N1 . . -177.5(2)
C1 N1 C3 C4 . . -178.4(3)
C1 N1 C3 C2 . . 0.4(3)
C2 C3 C4 C5 . . -1.2(4)
N1 C3 C4 C5 . . 177.5(3)
C3 C4 C5 C6 . . -0.2(4)
C4 C5 C6 C7 . . 1.4(5)
C5 C6 C7 C2 . . -1.2(4)
C3 C2 C7 C6 . . -0.2(4)
N2 C2 C7 C6 . . -177.4(3)
C13 C9 C10 C11 2_566 . -1.3(4)
C13 C9 C10 S1 2_566 . 178.19(18)
O3 S1 C10 C9 . . -118.6(2)
O1 S1 C10 C9 . . 120.9(2)
O2 S1 C10 C9 . . 2.0(2)
O3 S1 C10 C11 . . 60.9(2)
O1 S1 C10 C11 . . -59.6(2)
O2 S1 C10 C11 . . -178.54(17)
C9 C10 C11 C12 . . -179.5(2)
S1 C10 C11 C12 . . 1.1(3)
C9 C10 C11 C11 . 2_566 1.1(4)
S1 C10 C11 C11 . 2_566 -178.4(2)
C10 C11 C12 C13 . . -179.7(2)
C11 C11 C12 C13 2_566 . -0.2(4)
C11 C12 C13 C9 . 2_566 0.4(4)
